


I've Got You

by Nikolaus_Chaser



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Caring Castiel, Creampie, Dirty Talk, First Time Bottoming, Fluff and Smut, Insecure Dean, M/M, Size Kink, Sweet Castiel, Top!Cas, bottom!Dean
Language: English
Status: Completed
Published: 2015-12-02
Updated: 2015-12-02
Packaged: 2018-05-04 11:02:42
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,069
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5331788
Author URL: https://archiveofourown.org/users/Nikolaus_Chaser/pseuds/Nikolaus_Chaser
Summary: <blockquote class="userstuff">
              <p>
  <i><b>Prompt Request:</b> Dean being nervous to bottom for the first time. He's been pacing the bunker all day, a nervous-wreck waiting for Cas to come home. And when Cas steps in the door way he looks at Dean and Dean cowers. Castiel, being the sweetheart angel he is, picks him up in his arms and carries them to the bedroom. Castiel lays Dean out and slowly, lovingly stretches him, soothing every little whimpering Dean makes, telling him 'it's okay, I've got you.' And when Cas fucks him, Dean is begging to go harder.</i>
</p>
            </blockquote>





	I've Got You

Dean wasn't really sure about this.

In fact, he was starting to regret this.

Really, really regret it.

When Cas had first asked if he wanted to try bottoming for the first time, all sweet smiles and fluttering lashes and persuasive touches, Dean had been fully on board. How could he not have been? Castiel had that affect in him where he could just turn Dean into a soft, gooey mess that would do anything Cas asked of him.

But now- a week later and the date the two of them had agreed would be Dean's first time- Dean wasn't feeling so hot about the whole arrangement. I mean, this was his ass they were talking about. _His ass_ , which Cas wanted to put his dick into. And Cas's dick was pretty big, if Dean recalled. He involuntarily shivered at the thought of it.

Cas wasn't home right now to see the nervous wreck that Dean had become, thank God. He and Sam had left for a quick salt and burn a few days before, and we're now on their way home. He'd received a text from Cas little more than half an hour ago to let him know that he and Sam had just crossed the border from Nebraska into Kansas, and would be home in two or three hours. Along with that text had come another, more explicit message, about how Castiel couldn't wait to 'fuck Dean into the bed' that night.

That had been the onset of Dean's panic, if he was going to be honest. Because he already hadn't been too sure about the whole deal before, but now he knew that Cas was looking forward to this. Cas _wanted_ this, and didn't Dean owe it to him to at least give him what he wanted? Didn't he owe it to him to make it good? 

His hands shaking slightly, Dean felt himself walking into the bathroom and stripping down, until he was naked. Then he clambered into the shower and turned the water on, letting it run down his back. He knew that if he was going to do this for Cas, he was going to have to prep himself beforehand. After all, he was used to prepping Cas before they had sex. And he really _did_ want to do this for Cas, even if he himself didn't really want to do it. So, taking a deep breath, Dean reached around behind himself and pressed a finger against his tight hole. He let out a very unmanly squeak as the tip of his finger breeched his hole, and it burned. He drew in a ragged breath, wondering how on earth Cas could ever find pleasure in this, before he forced himself to continue.

By the time he got his entire finger into his ass, the pain from the stretch was nearly unbearable. He braces himself against the wall and grunted loudly, pumping his finger in and out as best as he could. But he was so tight, and tense too, and the only thing that fingering himself seemed to be doing was making his stomach tighten- and not in a good way. Finally he decided that enough was enough, and he withdrew his finger from his ass, turning the water off and climbing out of the shower. He'd just have to wait until Cas got home to prep himself.

Dean busied himself by making dinner, nearly burning himself twice and almost burning the empanadas that he was cooking, his mind was wandering so much. He just couldn't get over how painful it had been to put just one finger up his ass, and was horrified by the idea that Cas was going to try to fit his cock up there. Cas's cock, which was nearly 8 inches long soft and proportionally as thick. Dean dropped the saucepan he was holding on the floor and watched as half-fried peppers and onions splattered all over the kitchen floor.

By the time that Sam and Cas got home, it was dark out. The three of them ate at the kitchen table together, Sam and Cas chattering away about the hunt and how the ghost had been some sort of serial murderer from the 1930's. Dean didn't talk much- actually, he didn't talk at all. But neither Sam nor Cas seemed to notice how uneasy Dean looked, and for that he was grateful.

San yawned loudly around ten o'clock, stretching his long arms over his head. "I'm exhausted. Going to go sleep for about a year," he said, pushing his chair back and standing up. Dean nodded in his direction and offered a small, weak smile as Cas looked up at him.

"Goodnight, Sam. I think we'll be getting to bed as well," he smiled as he stood up, reaching for Dean's hand. Dean took it, squeezing Cas's fingers just a bit too tightly as he felt his heart leap into his throat.

"Night, guys." Sam said, walking away. Dean swallowed and looked away from Cas, who was staring at his face, and opted to look down at the floor instead.

"G'night, Sammy." He mumbled. And then he and Cas were turning away, were walking towards the bedroom. Dean didn't even realize he was shaking until Cas stopped hem in the doorway of the bedroom, cupping Dean's face.

"Dean, are you okay? You're trembling." He asked, frowning. Dean's cheeks turned bright red, and he felt like crying. Instead, he cleared his throat and shook his head.

"I'm fine, Cas. Let's just... Let's do this." He said, smiling weakly and tugging Cas towards the bed. Castiel didn't move though, frowning at his lover.

"Dean, I don't want you to do anything you're uncomfortable with. If you've changed your mind about this-"

"No, Cas. I want to do this. I want to give this to you." He swallowed, feeling his stomach flip at his own words. "I want you to... To..."

"You can't even say it, Dean..."

"Yes I can! I want you to fuck me, Cas, okay? I want you to- to shove your cock into me and pound me into the bed, okay? I want to give you what you want."

Castiel frowned and stepped forward, gesturing for Dean to sit on the bed. He did so and Cas joined him momentarily, taking Dean's hands into his own.

"Dean, I don't want any of those things. I don't want to simply 'fuck' you or 'pound you into the bed'. I want to..." He paused, searching for the right words. "I want to ravish your body. No, I want to worship your body. I want to kiss every inch, every freckle, and give you every ounce of pleasure that I possibly can." He sighed. "I was very much looking forward to penetrating you tonight. But I would never want to do that to you if it made you uncomfortable. I don't take pleasure in making my partners do things they don't want to."

Dean's cheeks turned red again and he looked down at the bed. "I know you don't." He mumbled, picking at the thread on the sheets. "I just..." He swallowed. "I'm scared it'll hurt." He whispered shamefully. 

Castiel's fingers tightened around his, and when Dean looked up he was expecting Cas to laugh at him. Or maybe to sneer; to roll his eyes and tell Dean that he was being a baby. What he didn't expect was to see Cas smiling softly at him, a gentle look in his bright blue eyes.

"It will hurt, at first. But I promise that, if you allow me, I will go slowly. I'll make it pleasurable." He leaned forward, his lips ghosting over Dean's for a moment, breath tickling Dean's lips. His breath hitches and he licked his lips, leaning forward and meeting Cas's lips in a warm, soft kiss.

Dean's entire body seemed to relax as he kissed the angel, melting against his body and deepening the kiss. It was still slow; undemanding, but there was a certain heat behind it that had Dean's cock twitching to life in his pants. He sighed and wrapped his arms around Cas's neck, sticking his tongue out and probing at Cas's lips, sticking his tongue in and kissing him.

"I love you, Dean," Castiel breathed when they finally pulled apart, his fingers ghosting over Dean's jawline and down his neck. "Let me take care of you."

"Yeah," Dean breathed, closing his eyes and letting Castiel lay him down on the bed. He heard some shuffling and opened his eyes, happily greeted by the sight of Cas, shirtless. He smiled and reached out, grabbing on to Cas's bicep as the angel draped himself over Dean's body and kissed at his neck lazily.

Dean sighed and tilted his head back, exposing his neck to Cas's soft kisses and gentle nips. His fingers stroked over Cas's shoulders and back, gentle touches that had Cas humming appreciatively against Dean's neck, sucking a little harder maybe as he made his way down to his collarbone.

"Can I undress you?" Castiel asked, his voice gravelly against the hallow of Dean's neck. Dean let out a soft noise from the back of his throat and nodded.

"Yeah." He breathed, leaning up to kiss Cas's lips. He moaned and kissed back, opening his mouth for Dean's tongue and reaching in between them, deftly unbuttoning his plaid shirt to reveal a Henley underneath. Castiel snorted.

"You're wearing so many clothes." He murmured. Dean blushed and shrugged.

"Like I said, I was scared." 

"Don't be." Castiel whispered, his breath ghosting over Dean's collarbone as he finally freed him from the button-down. He pushed it away and sat up, pretty much straddling Dean's lap as he tugged at the hem of his shirt.

"I'm not, anymore." Dean said, Adam's apple bobbing in his throat. "I don't think so, anyway. Not with you." As he spoke he let his fingers trace the cleft of Cas's jaw, over his scratchy stubble. Castiel smiled and leaned down to kiss Dean's again, finally managing to tug the Henley over Dean's shoulders. The man fell back onto the bed with a grunt, reaching out to pull Cas down for another kiss.

"Love you, sweetheart." Dean murmured against Cas's lips, a smile tugging at his lips. Castiel felt warmth blossom in his chest and he grinned, continuing to kiss Dean languidly as he reached between them to tug at Dean's belt.

"No panties for me today?" Castiel teased as he popped open the button of Dean's pants, revealing plain gray boxers. Dean rolled his eyes.

"Oh, shut up and fuck me already." He snapped. Castiel laughed, happy and free, leaning down to slot his and Dean's mouths together. The kiss was wet; messier than the others had been, but Dean didn't mind. He simply pressed his fingers into Cas's back, arching up to rub his growing election against Cas's leg. Castiel returned the sentiment, rolling his hips down and revealing the hard press of his cock through his jeans.

"Oh, baby." Dean gasped, titling his neck back so that Cas could suck at it as he lifted his hips, shimmying out of his jeans with the angel's help. 

Systematically they removed each other's clothing, pulling off each article with enthusiasm, only stopping once they were both in their underwear. Dean's breath hitched as he felt the palm of Cas's hand brush his cock, and he swallowed nervously despite himself.

"Almost there." He laughed, trying to cover up the fact that he was starting to get nervous again. Because Cas's cock was right there under his boxers, hard and heavy against Dean's leg. And Dean was going to take it up his ass, and it was going to hurt.

"Maybe I should get the lube." Castiel whispered, shuffling up to a sitting position and sliding off of Dean's lap. Dean grabbed his wrist before he could go, looking up at him with big green eyes. Castiel leaned down and kissed him reassuringly, smiling against his lips. "I'll be right here, honey. I'm not going anywhere."

Dean seemed to relax a little more after that, closing his eyes and counting to five before he got up and shuffled into a new position on the bed, now propped up by pillows. When Castiel returned to the bed he was all smiles, crawling over to Dean and kissing him gently.

"This is going to feel very nice, Dean. I promise." 

"For you or for me?" Dean mumbled under his breath, not meaning for Cas to hear. Still the angel only leaned forward to kiss Dean once again, cupping his face.

"For both of us." He said, pecking Dean's lips one more time. "I promise... Now, can I remove your boxers?"

Dean smiled a little and nodded, laying back and spreading his arms out around him. He wiggled his hips a little when Cas reached forward to tug at the hem. Castiel laughed and pulled at the fabric, pulling down do that Dean's cock could spring free, hard against his thigh. Cas smiled and reached forward, wrapping his fingers around the shaft and stroking up and down. Dean sighed and closed his eyes.

"There you go," Castiel whispered, leaning down to press a kiss to the head of Dean's cock. The man gasped, his eyes popping open and watching Cas with rapt attention as he opened his mouth around the head of his cock, sucking him down. His mouth was warm and wet around Dean's cock and he moaned, throwing his head back against the pillows.

"Oh, God." Dean called out, tangling his fingers into Cas's hair. "Oh, baby."

Castiel hummed around Dean's cock and flicked his tongue over the slit, slowly popping open the bottle of lube in his hands and squirting a generous amount into his palm. He rubbed his hands together to warm it up, knowing from his own experience that cold lube did not feel good.

Bobbing his head up and down and swirling his tongue around the head of Dean's thick cock, Castiel carefully pressed his index finger against Dean's hole. He was pleased to find his muscles relaxed, though they tensed up almost as soon as Cas pressed up against him.

Castiel pulled off of his cock, letting out a puff of breath against his dick. "Relax, Dean. We're taking this nice and slow."

Dean let out a heavy sigh. "Okay." He breathed, letting out all the air in his body and sinking back into the sheets. Castiel smiled and kissed the head of his cock, carefully easing his index finger into Dean's hole. Dean's toes curled but other than that he stayed relaxed, his cock still hard where it laid against Cas's chin.

"That's a good boy." He whispered, easing his finger in and out of Dean's hole. Dean's cock pulses at Castiel's words, a shiny pearl of precum running down the side of his cock. Cas quickly lapped it up, twisting his finger inside of his lover. Dean gasped, his legs jerking against the bed. Cas looked up at him, smiling softly.

"How're you doing?" He asked as he slowly began to stroke Dean's cock, pumping up and down in time with his thrusts. Dean sighed.

"Good. Okay, I think. It feel weird."

Castiel pressed a kiss against his thigh, twisting his finger again. "Good weird, or bad weird?"

Dean swallowed and sat up a little, shrugging. "I don't know. Just... Weird."

"Okay." Castiel pressed another kiss to his thigh, letting go of his cock and picking up the lube. "I'm going to add another finger. Is that alright?"

"I guess." Dean said. Castiel smiled and poured some lube on to his fingers, then carefully eased a second one in alongside his index finger. Dean grunted and involuntarily pushed back against the fingers, causing Cas to fuck deeper into him.

"Shit," he breathed out. Cas immediately stopped moving his fingers, looking up at Dean.

"Are you okay?"

"Yeah, I'm fine." Dean insisted, flashing Cas a smile and wiggling his hips. "Just didn't expect to feel so full."

Castiel chuckled and pressed a kiss to Dean's thigh, pumping his fingers slowly. "Yeah, it's an odd sensation at first. You'll get used to it."

"Doubt it," Dean breathed out, closing his eyes and letting his body relax. Castiel really was being gentle about this, taking his time, and it was with a blush that Dean had to admit to himself that he was enjoying this. Enjoying the attention. _Enjoying Cas's fingers in his ass._ he let out a strangled moan when he felt Cas's fingers brush over that sensitive nub inside of him. 

"Goddamn..." Dean moaned as Cas brushed over the spot again, and he arched his back, pushing down on the angel's fingers. "Now I know why you like doing this so much..."

Castiel laughed at that, withdrawing his fingers from Dean's ass and picking up the lube again. Dean made a noise of protest; a little whine in the back of his throat, but Castiel quickly shushed him.

"I just need more lube, baby. I'm going to try three fingers now."

"Please." Dean moaned, his eyes fluttering shut when he felt Cas's fingers at his hole once again. He worked in one, then two, and finally once he was taking two easily again he started to push the third one in. Dean groaned at the feeling of being so full; so stretched, grasping at the sheets.

"C-Cas, I..." He whimpered, wiggling his hips. Cas quickly reached up and took hold of his cock, which was starting to soften, pumping it back to full hardness. Dean moaned, half pain and half pleasure, his chest heaving.

"It's okay, I've got you." Cas whispered, and though Dean knew that he was down by his ass, it felt like he was right there in his ear, a reassuring presence that would make everything okay. He let out a strangled moan, arching his back.

"It feels... Ah, Cas, I never thought it would feel so... So good..." He cut off on another moan when Cas started to brush his prostate again, the pleasure overwhelming any pain he once felt.

"I'm glad you're enjoying yourself." Castiel murmured, scissoring his fingers once and continuing to pump them in and out. Dean whimpered.

"More, Cas. I can take... I can do it."

"I know you can, baby. Just wait..." He murmured, scissoring his fingers again and stretching Dean's rim wide. Once he deemed him ready he pulled back, watching Dean's hole flutter desperately around fingers that were no longer there. He shuffled forward so that he was on his knees, bulging cock evident through his see-through underwear. He quickly disposed of the garment, taking his flushed cock into his hand and wetting it with lube.

"Just relax, Dean." Castiel whispered as he lined his cock up to Dean's loose hole, the red and bulbous head already catching on his rim. Dean seemed to flutter around him, and it took all the self-control Castiel had not to push right in and fuck Dean into the mattress. No, he was going to make this good for Dean. So instead he gripped his cock, almost three inches wide, and slowly began to push in. Dean's hole spread around his head, sucking him in. He was tight and hot around him, his rim stretched to its max, and with only the head of his cock inside Cas felt like cumming. He moaned loudly and leaned forward, grabbing Dean's hips and pulling him closer; plunging his cock further into Dean's tight body.

"Cas," Dean gasped, reaching up and wrapping his fingers tightly around his biceps. Cas moaned out Dean's name in response, his head dropping to rest of Dean's shoulder.

"Are you okay?"

"You're so big," Dean moaned out, his chest heaving as his rim continues to flutter around Cas's thick cock. It was almost too much for his body to handle, the stretch, and he found himself spreading his legs wider for the angel. "I feel so full."

Cas groaned, his cock pulsing inside of Dean. He looked down at his crotch, where he and Dean were joined. To see that his cock wasn't even halfway buried in the hunter. Not even halfway and he was already ready to cum. He drew in a shaky breath, kissing Dean's lips softly. 

"I'm going to keep going."

"Fuck." Dean moaned and let his head fall back, let his mind float away as he felt Cas digging fingers into his hips and pushing his hips forward. His rim was stretched obscenely around Cas's thick cock, the size of it almost unreal, and he could feel Cas trembling above him. He moaned in the angel's ear, fingers digging into his shoulder blades.

"More, Cas. I can take more." He growled out. Castiel groaned and thrust his hips forward once more, now buried balls deep inside of his lover. . He paused then, looking down at where they were joined together. He could have sworn his cock was so big inside of him that he could see it in his stomach, but he knew that that wasn't possible. Still, the thought made him pulse inside of Dean, and once again he felt like he was going to cum. He looked back up at Dean's face, striking a hand over his hip affectionately.

"I'm going to move." He gasped, voice all gravel and sex. Dean moaned.

"Go ahead, Cas. Move." He gasped. Castiel let out an inhuman noise from the back of his throat as he withdrew his cock from Dean's hole, then slowly thrust back in. Dean moaned, practically clawing at Cas's back as his hips began to piston forward over and over again.

"So tight, Dean. You're so tight I-" He moaned and moved his hips faster, thrusting deep into Dean's ass and then pulling back again. The sound of skin slapping against skin filled the room, along with the sound of Dean's moans every now and then when Cas slammed against his prostate.

"Cas, my... My dick. Touch my dick." He gasped, tipping his head back. Cas moaned and leaned in, mouthing at his neck as he reached between them to grasp his hard cock.

It wasn't long before Dean was cumming. All Cas had to do was angle his thrusts at Dean's prostate and press his thumb against the hunter's slit and he was cumming, screaming out loud as he coated both of their stomachs in thick globs of semen.

"Dean. _Dean._ " Castiel groaned as Dean tightened around him, his hole fluttering around Cas's cock and squeezing him like a vice. He cried out, biting at Dean's shoulder roughly as he spilled inside of him, his cock pulsing again and again as it filled him up with cum.

When he finally came down from his orgasm Castiel realized that he should pull out, and he eased his now softening cock from Dean's hole, careful not to hurt the man. His hole gaped back at Cas once he had removed his cock, cum leaking out and on to the sheets. Castiel squeezed his eyes shut as the sight made his oversensitive election twitch painfully, and he rolled over so that he was lying next to Dean.

"Hey, are you alright?" Castiel asked, reaching out and grasping Dean's hand. The man's green eyes fluttered open and he looked up at Cas, a slow smile creeping across his face.

"I don't think I've ever cum so hard in my life." He said hoarsely. Castiel laughed, smiling.

"I'll take that as a good thing. But I was referring to your cute little behind. Are you sore?"

Dean licked his lips and shrugged, a blush creeping up from his neck to his face. "Yeah, I guess. It's nothing really."

"Uh-huh." Castiel smirked, rolling over and straddling Dean's lap. He kissed the blush on Dean's cheeks, smiling broadly at him as he did so. Dean rolled his eyes and pushed the angel away, turning his head. Castiel laughed, kissing Dean once more before rolling off of him.

"I would go to the bathroom, if I were you."

"Uh, yeah. Right." Dean muttered, slowly getting out of bed. He stretched his legs, then stood up and made his way to the bathroom. As the door closed, he could hear Castiel shouting.

"And then you come right back to this bed, mister! You owe me some serious cuddle time."


End file.
